7664-66-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Isopropoxyaniline is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the formation of carbon-nitrogen bonds, which are crucial in the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 4-Isopropoxyaniline serves as an essential intermediate in the production of various agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Organic Chemistry Research:
4-Isopropoxyaniline is utilized as a reagent in organic chemistry reactions, particularly for the formation of carbon-nitrogen bonds, which are vital in the synthesis of complex organic molecules and have significant implications in advancing chemical research and development.

InChI:InChI=1/C9H13NO/c1-7(2)11-9-5-3-8(10)4-6-9/h3-7H,10H2,1-2H3

Upstream product

• 26455-31-2 1-isopropoxy-4-nitrobenzene 
• 100-17-4 para-methoxynitrobenzene 
• 7146-61-4 N-(4-isopropoxyphenyl)acetamide 
• 100-02-7 4-nitro-phenol 
• 135049-82-0 1-iodo-4-(propan-2-yloxy)benzene 
• 6967-88-0 1-bromo-4-isopropoxybenzene 
• 683-60-3 sodium isopropylate 
• 540-37-4 p-aminoiodobenzene 
• 106-40-1 4-bromo-aniline 
• 106-47-8 4-chloro-aniline 
• 73010-54-5 4-isopropoxy-4-methoxycyclohexa-2,5-dien-1-one 
• 150-76-5 4-methoxy-phenol 
• 622-62-8 4-Ethoxyphenol 
• 7495-77-4 4-isopropoxyphenol 

Downstream Products

• 107154-14-3 thioisonicotinic acid-(4-isopropoxy-anilide) 
• 7146-61-4 N-(4-isopropoxyphenyl)acetamide 
• 84308-82-7 N-(4-isopropoxy-phenyl)-N'-phenyl-acetamidine 
• 101785-50-6 N-(4-ethoxy-phenyl)-N'-(4-isopropoxy-phenyl)-thiourea 
• 87672-31-9 N-(4-Isopropoxy-phenyl)-isonicotinamidine 
• 95359-85-6 2-(4-Isopropoxy-phenylimino)-malonic acid dimethyl ester 
• 94256-99-2 2-(4-isopropoxyphenylamino)naphthalene-1,4-dione 
• 94257-65-5 2-(4-isopropoxyphenylamino)-3-chloro-1,4-naphthoquinone 
• 948552-60-1 C₁₀H₁₂ClNO₂ 
• 947240-29-1 N-(4-isopropoxyphenyl)-2-bromoacetamide 
• 241499-49-0 (4-Isopropoxy-phenyl)-(3-methyl-but-2-enyl)-piperidin-4-yl-amine 
• 241499-47-8 4-(4-isopropoxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 241499-48-9 4-[(4-Isopropoxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester 
• 902169-61-3 3-(4-isopropoxyphenylamino)pent-2-enedioic acid diethyl ester 

Relevant academic research and scientific papers

Crystallography-guided discovery of carbazole-based retinoic acid-related orphan receptor gamma-t (RORγt) modulators: insights into different protein behaviors with “short” and “long” inverse agonists

A series of 6-substituted carbazole-based retinoic acid-related orphan receptor gamma-t (RORγt) modulators were discovered through 6-position modification guided by insights from the crystallographic profiles of the “short” inverse agonist 6. With the increase in the size of the 6-position substituents, the “short” inverse agonist 6 first reversed its function to agonists and then to “long” inverse agonists. The cocrystal structures of RORγt complexed with the representative “short” inverse agonist 6 (PDB: 6LOB), the agonist 7d (PDB: 6LOA) and the “long” inverse agonist 7h (PDB: 6LO9) were revealed by X-ray analysis. However, minor differences were found in the binding modes of “short” inverse agonist 6 and “long” inverse agonist 7h. To further reveal the molecular mechanisms of different RORγt inverse agonists, we performed molecular dynamics simulations and found that “short” or “long” inverse agonists led to different behaviors of helixes H11, H11’, and H12 of RORγt. The “short” inverse agonist 6 destabilizes H11’ and dislocates H12, while the “long” inverse agonist 7h separates H11 and unwinds H12. The results indicate that the two types of inverse agonists may behave differently in downstream signaling, which may help identify novel inverse agonists with different regulatory mechanisms.

C-H Amination of Arenes with Hydroxylamine

This Letter describes the development of a TiIII-mediated reaction for the C-H amination of arenes with hydroxylamine. This reaction is applied to a variety of electron-rich (hetero)arene substrates, including a series of natural products and pharmaceuticals. It offers the advantages of mild conditions (room temperature), fast reaction rates (30 min), compatibility with ambient moisture and air, scalability, and the use of inexpensive commercial reagents.

Rationally Designed Polypharmacology: α-Helix Mimetics as Dual Inhibitors of the Oncoproteins Mcl-1 and HDM2

Protein–protein interactions (PPIs), many of which are dominated by α-helical recognition domains, play key roles in many essential cellular processes, and the dysregulation of these interactions can cause detrimental effects. For instance, aberrant PPIs involving the Bcl-2 protein family can lead to several diseases including cancer, neurodegenerative diseases, and diabetes. Interactions between Bcl-2 pro-life proteins, such as Mcl-1, and pro-death proteins, such as Bim, regulate the intrinsic pathway of apoptosis. p53, a tumor-suppressor protein, also has a pivotal role in apoptosis and is negatively regulated by its E3 ubiquitin ligase HDM2. Both Mcl-1 and HDM2 are upregulated in numerous cancers, and, interestingly, there is crosstalk between both protein pathways. Recently, synergy has been observed between Mcl-1 and HDM2 inhibitors. Towards the development of new anticancer drugs, we herein describe a polypharmacology approach for the dual inhibition of Mcl-1 and HDM2 by employing three densely functionalized isoxazoles, pyrazoles, and thiazoles as mimetics of key α-helical domains of their partner proteins.

A new ligand for copper-catalyzed amination of aryl halides to primary(hetero)aryl amines

N,N′-Bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide was found as a new ligand for copper-catalyzed amination of aryl iodides, bromides and chlorides to afford various primary (hetero)aryl amines. These reactions proceeded efficiently under mild conditions when inexpensive aqueous ammonia (28% NH3 in H2O) was used as the amino source.

Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?

The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.

Intermolecular C–O Coupling Using Hemicucurbituril Supported Ionic Liquid Phase Catalyst

Abstract: Hemicucurbituril supported ionic liquid phase catalyst (HmCucSILP) has been synthesized by anchoring multilayer of ionic liquid ([Bmim]Cl) containing Pd(OAc)2 and X-phos on the surface of hemicucurbit[6]uril. The HmCucSILP was effectively employed in intermolecular C–O coupling of aryl halides with sodium alkoxides for the synthesis of alkyl aryl ethers. Graphical Abstract: [Figure not available: see fulltext.]

Direct synthesis of anilines and nitrosobenzenes from phenols

A one-pot synthesis of anilines and nitrosobenzenes from phenols has been developed using an ipso-oxidative aromatic substitution (iSOAr) process. The products are obtained in good yields under mild and metal-free conditions. The leaving group effect on reactions that proceed through mixed quionone monoketals has also been investigated and a predictive model has been established.

Synthesis and Biological Evaluation of N-Alkoxyphenyl-3-hydroxynaphthalene-2-carboxanilides

A series of fifteen new N-alkoxyphenylanilides of 3-hydroxynaphthalene-2-carboxylic acid was prepared and characterized. Primary in vitro screening of the synthesized compounds was performed against Staphylococcus aureus, three methicillin-resistant S. aureus strains, Mycobacterium tuberculosis H37Ra and M. avium subsp. paratuberculosis. Some of the tested compounds showed antibacterial and antimycobacterial activity against the tested strains comparable with or higher than that of the standards ampicillin or rifampicin. 3-Hydroxy-N-(2-propoxyphenyl)naphthalene-2-carboxamide and N-[2-(but-2-yloxy)-phenyl]-3-hydroxynaphthalene-2-carboxamide had MIC = 12 μM against all methicillin-resistant S. aureus strains; thus their activity is 4-fold higher than that of ampicillin. The second mentioned compound as well as 3-hydroxy-N-[3-(prop-2-yloxy)phenyl]-naphthalene-2-carboxamide had MICs = 23 μM and 24 μM against M. tuberculosis respectively. N-[2-(But-2-yloxy)phenyl]-3-hydroxynaphthalene-2-carboxamide demonstrated higher activity against M. avium subsp. paratuberculosis than rifampicin. Screening of the cytotoxicity of the most effective antimycobacterial compounds was performed using THP-1 cells, and no significant lethal effect was observed for the most potent compounds. The compounds were additionally tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. N-(3-Ethoxyphenyl)-3-hydroxynaphthalene-2-carboxamide (IC50 = 4.5 μM) was the most active PET inhibitor. The structure-activity relationships are discussed.

INHIBITORS OF BRUTON'S TYROSINE KINASE

This application discloses compounds according to generic Formula (I): wherein all variables are defined as described herein, which inhibit Btk. The compounds disclosed herein are useful to modulate the activity of Btk and treat diseases associated with excessive Btk activity. The compounds are useful for the treatment of oncological, auto-immune, and inflammatory diseases caused by aberrant B-cell activation. Also disclosed are compositions containing compounds of Formula I and at least one carrier, diluent or excipient.

SUBSTITUTED TRICYCLIC COMPOUNDS WITH ACTIVITY TOWARDS EP1 RECEPTORS

The present invention belongs to the field of EP1 receptor ligands. More specifically it refers to compounds of general formula (I) having great affinity and selectivity for the EP1 receptor. The invention also refers to the process for their preparation, to their use as medicament for the treatment and/or prophylaxis of diseases or disorders mediated by the EP1 receptor as well as to pharmaceutical compositions comprising them.